This may be old news by now, but I've been thinking about "the ones that got away."
I'm with Jason: go for the one you love to play. I'm still kicking myself about the classical guitar I picked up on a whim and didn't want to put down. I should have put it on layaway and figured out how to buy it later. Same with a used Les Paul Studio. They were great instruments -- both sold before I could get back to look at them again.
Here's a crazy thought no one mentioned: set up. I started my guitar playing on a Squier by Fender Affinity Series. It was from the 90s, and higher quality than the current models. My guitar teacher did a fret level as part of the set up and I grew to love it so much that I couldn't find a guitar anywhere that matched it for playability. I wore the frets down and it's not worth paying someone else to refret it, unfortunately.
The rub in this case is that the set up on most new guitars I've tried to play is really awful, so I never enjoy playing them in a store.
I've 'replaced' the Squier with a high-end Japanese guitar. The major differences? The sound of the pickups, the shape of the neck and the Floyd Rose copy bridge.
I bought a used LPS on Reverb. It spends most of its time in the case. It's not the same as the one I played in the store.
So, again with Jason: Strat/strat copy (my guitar teacher was a blues guy and he owned four) or the Les Paul.
Play it. And buy it because you love playing it.
Oh, and because you probably have been playing your Tele for awhile... how's it going?